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LEAVING IS THE HARDEST PART

No more planning or worrying I hadn’t packed an essential item. All I really needed was my bike, tent, and sleeping bag—as Ray Jardine would say, “If you don’t have it, you don’t need it.”

With a belly full of Portland’s finest burrito, it was time to pedal out of the city and into the hills, toward the coast. Out of the trees, down to the ocean, the mist rolled in and the Oregon Coast started to take shape, revealing damp roads surrounded by moss and rusty trucks.

I decided to take a scenic turnoff called “7 Devils Road.” Expecting a leisurely cruise with ocean vistas, I found the steepest climb of my entire ride. After a painful 20 minutes to the top, there was a hand-painted sign on the road that read “Devil #1,” and suddenly it clicked… there were going to be 6 more of these brutal ascents. By Devil #6, it was time for a scenic coffee break—a perfect opportunity to watch broken bikers trudge by. This place seemed to be every traveler’s traumatic zenith. Everyone I met from here on had a story to tell about battling the 7 Devils.

The first storm hit just north of the California border, and my soaked gear was a precursor to the rest of the trip. I eventually landed at a timeless motel just off the highway, where I discovered a slew of sodden bikers looking for shelter. While resting in the motel bakery, I heard rumors of a church that hosted bike tourers.

NORTHERN CALIFORNIA

I rolled up to a local supermarket at the same time as a group of dirtbag folks who could only be seasoned bike tourers. A burly Australian, with a wilier beard than my own, started chatting with me (as bearded folk usually do), and we quickly made plans to cook dinner and drink beer back at the church. Over bowls of pasta, we compared horror stories of the previous night’s storm, only to move on to the lighter topic of how much food we could consume… our hunger obviously some sort of superpower.

The church held a hoi polloi of bike-loving folk, and about 20 of us could sleep on the floor, the only rule being we had to be out on Friday mornings for Katie’s knitting group. There was a German scientist sleeping in his tent, a French couple who were touring with their Rottweiler in a trailer, and a guy from Portland who introduced me to his daily diet of “peanut butter soup” (trail mix poured into an industrial-sized peanut butter jar, and eaten with a spork).

The comforts of this place lulled weary travelers, retaining most longer than they had planned. Eventually, after laundry, showers, and beer-fueled night rides, a group of us decided to ride south together through the Redwoods and down to Arcata. There were rumors of a killer burrito shop there, and it seemed like there we would part ways.

Our group included Ben, the bearded Australian, who always carried a six-pack in his basket; Evie, from Bellingham, the coolest sci-fi writer I’ve ever met; Richard, the peanut butter soup creator from Portland, who quickly earned the nickname “Portland”; Tommy, a well-equipped bike mechanic with killer pancake-making skills; and myself. Richard and Ben pulled trailers, and Ben had a surfboard on his. We were clearly a rowdier bunch than your average bike-touring group. The Redwood Orphans were born.

THE ORPHANS

The trees became giants as we rode into the saturated air of the Redwoods, hooting and hollering at each other like a pack of wolves, carving lines on the damp asphalt and red-mulched shoulder. We passed tourist haunts and parked luxury RV trailers, lined up for designated photo spots along the highway, and played catch-up with the tourist vans. We were keen to know what the must-sees were. We got to see the whole picture… we were in it, absorbing everything the landscape had to offer. The macro moments that the bikes allowed were the biggest distraction from our ride than anything else… from the magnificence of an ancient redwood, to nearly microscopic moss on the side of the road.

We ate pancake and coffee breakfasts, slept in piles like wild dogs, and lounged under tarps strung together with bungees and old ropes. We fought off gangs of raccoons, while eating s’mores around campfires, and waited out downpours in diners, while our dripping jackets and gloves hung from every available space. We shared everything—we were cycle siblings—and always ended the day with a hoppy brew. The Orphans rolled into camp late and left early before the rangers started their daily rounds. Hiding a group of five took a bit of planning, but we always managed to create shanty camps wherever we ran out of steam. Other bike tourers heard of our clan, as well as our reputation for coffee breaks, beards, peanut butter soup, and how we road-raged the miles away. Word obviously traveled fast in the biker community.

As the days warmed up and we ditched the merino layers, the tailwinds blew us south on shoulder-less Highway 1 toward San Francisco. We held our own as we picked tight lines, inches between speeding trucks and the cliff edge. Angry motorists raised their fingers, pissed that we’d chosen two wheels over four.

The Orphans scattered in different directions before we reached the Golden Gate Bridge, and while we parted without so much as a “so long” or “farewell,” we were certain we’d cross paths again. A flat tire or stop at a burrito shop could mean you wouldn’t see someone again for weeks. Tommy and I awoke to the sunrise over the Golden Gate one morning, and crossed the bridge in the busy bike lane with Alcatraz in the hazy distance.

SAN FRANCISCO

San Francisco was as good as I imagined it would be. New York-style pizza served to a metal soundtrack, coffee, bakeries on every corner, bike lanes leading anywhere, and hillier hills than I rode the whole trip. It was the first time I nearly broke my “no stopping on hills” rule. It was Halloween, and the Orphans re-connected for a Halloween Critical Mass bike ride through the city. There were about 300 riders. We parted ways over cheap margaritas at a taco shop, and I headed south toward Santa Cruz. I stopped there for a week with a bearded coffee shop barista before riding into the epic landscape of Big Sur.

Riding obliviously into the coastal wilderness, I stopped at a burrito shop in Big Sur to demolish, I later discovered, my last hot meal for days. I’d made my way into California’s jewel. It was a 100-mile stretch of vast cliffs, canyons, and wild ocean roads that clung to sheer hills. There was no visible population, no park rangers, no stores with food supplies—not even any other bike tourers. It was just an endless fleet of touring RVs towing cars, boats, and motorcycles to every sign that promised a majestic photo-op. They were exploring the wilderness from the comfort of their home on wheels, which they would later reminisce about.

My food supply was low after the first day, so I rationed the last of my nuts, dark chocolate, and tin of chickpeas, which I used as fuel to conquer the physically draining headwinds, peaks, and endless dips of unforgiving highway. It was hard pedaling and I needed presence for every rotation. The envious looks from the tourists in their cars had changed to pity, as I struggled like a dying mule through those last few punishing miles.

As Kerouac said about this place, “The more ups and downs, the more joy I feel. The greater the fear, the greater the happiness I feel.” It would be a while before I could identify.

THE LESSON IN BIG SUR

As the hills eased and I left Big Sur behind, I celebrated with a beer in some long grass before setting up camp in a cluster of trees. I woke up in the early hours to a dull thudding pain in my right arm. After hurried self-inspection, I saw a tick and its bundle of legs sticking out of me. It was dark, and after a failed attempt at removal, all I could do was sleep and wait to find someone who knew how to extract the beast.

It was a 15-mile ride to Cambria, the nearest town, and I had nothing to eat, howling headwinds, and a dead tick under a bloody scab on my throbbing arm. I was so grateful to the chill guy in an outdoor store who pulled the tick out while laughing at me.

When I hit the Southern Californian highways of Malibu and Santa Barbara, the days were warm and I felt like the sun always set too soon, as I pitched my tent and itched for the next day’s ride. The northern tailwinds eased me from expanses of farmland, rich with Mexican farm workers and dry red mountains, to perfect Californian point breaks and deep golden sunsets over the Channel Islands. At one point, I found myself in scenery that looked like a Baywatch episode—the lifeguard towers, beach volleyball, flashy cars, little dogs, vineyards, and Howard and Nancy in their gated community. It felt like a new era—so far from the hazy days of the Redwoods of Northern Cali. My soundtrack of Neil Young and Bill Callahan didn’t feel right anymore. The trees were eucalyptus or cactus plants, and it smelled more like the Australian Outback than North America.

Without warning, my camping days were over. I left Leo Carrillo State Park and stole a shower at a beach vista in the morning sun. I rolled closer to LA through Santa Monica Boulevard, and meandered along the promenade, passing the freaks of Venice Beach. I pushed on to San Diego to meet some old travel buddies who had a bed for me in Ocean Beach and a plan for a Mexican surf trip.

My ride was nearly done, and the fun part was long gone. It was just sprawling suburbs down to the border. The last stretch of my journey was getting down to the border and signing this trip off.

The Orphans were out there somewhere, and as I rolled up to the border gates and saw the Mexican flag blowing over Tijuana’s arch and its concrete sprawl, I knew it had all been worth it. I got one last burrito before heading back to San Diego, with dreams of learning some Spanish, taking on that border crossing, and anticipating the adventures that waited for me just beyond.